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Mole de Mayo
Photograph: Courtesy Star Events

The best free things to do in Chicago this month

No need to break the bank—check out all the fun (and free) stuff happening throughout the city this month.

Emma Krupp
Edited by
Emma Krupp
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As it turns out, some of the best things in life—or at least, some of the best things to do in Chicago—are free. May marks the unofficial start of summer festival season in Chicago, so prepare to hit the streets for food, drinks, live music and plenty of rollicking celebrations (note that while these are technically free, it's usually good form to toss in a small donation). Plus, don't miss out on gallery shows, concerts and other recurring events that won't cost you a dime. Ready to save some money? Check out more of the best free things to do in Chicago this month.

RECOMMENDED: The best cheap eats in Chicago

Time Out Market Chicago
  • Time Out Market
  • West Loop

Every Sunday from 11am to 3pm, Time Out Market Chicago's chefs offer a variety of delicious brunch dishes, from Hangover Ramen with shrimp and smoked pork to a stack of Buttermilk Pancakes layered with whipped mascarpone. Order as much as you want, grab a mimosa pitcher from the bar and stick around from 1 to 3pm for a set of tunes from the Chicago Soul Jazz Collective. 

The best free things to do in Chicago this month

  • Things to do
  • Fireworks
  • Streeterville

During the summer, one of the best aerial displays you'll find in Chicago originates from Navy Pier. The Chicago attraction hosts twice-weekly fireworks shows (on Wednesdays and Saturdays) from Memorial Day weekend through Labor Day weekend, with stunning views available from across the pier's public spaces. Of course, you can also take in the show from nearby beaches or while cruising along the Lakefront Trail.

  • Movies
  • Wrigleyville

Wrigley Field-adjacent plaza Gallagher Way is once again teaming up with the Music Box Theatre to program free outdoor movie screenings this summer. Admission is free and attendees are welcome to bring their own food, enjoy on-site concessions or snag a meal from nearby restaurants like Big Star and Smoke Daddy. VIP seating is also available for $30—check out the Gallagher Way website for more details. Gates open at 6pm for each screening and the movie starts at 7:30pm

May 11: Bill and Ted's Excellent Adventure
May 25: Rocketman
June 8: Mamma Mia!
June 22: Josie and the Pussycats
July 6: Dirty Dancing
July 20: School of Rock
July 27: Pitch Perfect
August 3: Grease
August 17: Encanto
August 31: Almost Famous
September 14: Selena
September 21: Bohemian Rhapsody

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  • Things to do
  • Festivals
  • Lower West Side

Pilsen's annual Mole de Mayo street festival—which honors the traditional Mexican sauce with a mole cook-off, plus a market full of vendors—returns to the neighborhood over Memorial Day weekend for its first in-person celebration since 2019. Grab some enchiladas smothered in aromatic mole and don't miss the festival's lucha libra wrestling matches. 

  • Things to do
  • Festivals
  • North Center

Ravenswood Corridor neighbors Dovetail and Begyle return to in-person celebrations this year for their annual Memorial Day weekend street fest on Malt Row, where attendees can sip beer from both breweries and grab snacks from Beard and Belly, El Zorro Tacos, Happy Lobster and more. Catch live music curated by CHIRP and consider tossing in a donation, which will benefit neighborhood food pantry The Friendship Center. 

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  • Things to do
  • Festivals

This annual festival—which returns in 2022 with a full slate of in-person events—assembles luminaries from the fields of politics, journalism and the arts for a multi-week series of programming across the city, with events ranging from lectures and discussions to screenings and musical performances. This year’s fest theme, ”Public,” explores how people might move forward with public and private life after two years of Covid-related isolation. Not everything on the calendar is free, but lots of the events (including talks with chef Kwame Onwuachi, writer Sheila Heti and more) won't cost you a dime. You can see a full schedule of programming on the Chicago Humanities Festival website

  • Art
  • Film and video

Projecting a 25-story-tall video installation on the side of the Merchandise Mart, Art on theMart's spring program focuses on two climate change-themed projections presented in partnership with the Shedd Aquarium. The first, Floe, was created by Chicago choreographer Carrie Hanson (in collaboration with her dance company, The Seldoms) and spotlights climate change through melting ice, extreme weather and the human body, set to soundscapes of icebergs, water and rain. The second, Choral, is by the collaborative localStyle and depicts the human impact on coral ecosystems.

Art on theMART's array of 34 digital projectors display the 30-minute program at 8:30 and 9pm every evening. The show is best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

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  • Music
  • Music festivals

Looking for free concerts near Chicago? Hop on the Blue Line to Rosemont's Parkway Bank Park for Thursday night performances—with a few holiday and weekend dates sprinkled through the summer—from classic rock cover bands like Yachtley Crew ('70s and '80s hits), Ticket to the Moon (Electric Light Orchestra) and Rush Tribute Project (Rush, obviously), complete with a fireworks show at the end of the night. Beverage tents will be located on site, but we won't fault you if you prefer to pre-game with a fishbowl-sized spiked punch from nearby Sugar Factory. For a full schedule of shows, visit the Parkway Bank Park website

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  • Art
  • Galleries
  • River West/West Town

Explore the housing crisis through the lens of artists like Gabrielle Garland, Tonika Lewis Johnson and Maymay Jumsai—as well as organizations such as the Southside Home Movie Project—in this Weinberg/Newton Gallery exhibit, a partnership with the nonprofit Mercy Housing Lakefront. Featured work includes paintings, collage, sculpture, video and large-scale installation, which tell the story of damaging housing practices while also imagining a more enriching, secure future for urban living. 

  • Art
  • Arts centers
  • Kenwood

Married artists Dutes Miller and Stan Shellabarger explore relationships, intimacy, queerness and loneliness during the Covid-19 pandemic in this immersive exhibition at the Hyde Park Art Center. Visitors can see three new works in the Art Center's gallery space—including a massive mural and a participatory installation that invites people to make their own paper cranes—and attend a number of free public programs, from a Pride-themed performance to a conversation with artist couples.  

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  • Things to do
  • Festivals
  • Greektown

Gather for a belated celebration of the 200th anniversary of Greek Independence Day—as well as all things related to Hellenic culture and identity—for the annual Greek Heritage Parade, which returns to Halsted Street for a day of in-person festivities. The parade steps off at 2:30pm, but attendees can also check out Greek vendors selling art, jewelry and gifts at the Greektown Agora (Elysian Field, Halsted and Van Buren St) and snap photos with Greek Warriors, or stick around for a performance from the Orpheus Dance Troupe at 5pm. 

  • Things to do
  • Festivals
  • Lake View

Love cover bands? Head to Lakeview (right by the Belmont Red Line station) for three days of music, featuring local tribute acts like Don't Speak, Fletcher Rockewell and Rod Tuffcurls & the Bench Press. A second stage hosts an eclectic array of community performers, including folks from the Japanese Cultural Center and local DJs accompanied by drag performers like Lucy Stoole, DJ Ca$hera, Irregular Girl and Tenderoni. Plus, you'll find beer, wine and plenty of area vendors to browse while you hang out on the street.

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  • Comedy
  • Uptown

This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.

  • Shopping
  • Markets and fairs
  • Bridgeport

Grab a cup of tea or a latte from this beloved Bridgeport coffee shop and mill around its annual springtime vendor bazaar, where you can shop goods like plants, stained glass, jewelry, stickers, candles and more. DJ This Margin Walker will provide music. 

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  • Things to do
  • Festivals
  • Lincoln Park

Say a hearty hello to summer at Mayfest, the annual street party in Lincoln Park that's outfitted with the usual selection of local vendors, tasty food, cover bands and ice-cold beverages.

  • Art
  • Painting
  • Loop

The Chicago Cultural Center hosts the first comprehensive retrospective of Robert Colescott, a 20th century American painter whose incisive, large-scale work took aim at racial inequities in America—among other social ills—with humor and wit. The exhibition examines Colescott's work throughout the decades, moving through the artist's stylistic evolutions from riffs on the Bay Area Figuration of the '50s and '60s to his graphic style of the '70s and beyond, as well as his role in bolstering Black representation in art.  

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  • Shopping
  • Markets and fairs

Originally established in the late 1800s, the Maxwell Street Market brought vendors, musicians and cooks to an open-air flea market where shoppers could find just about anything they wanted. The market introduced the Maxwell Street Polish sausage, provided a venue for rising Chicago blues musicians and was immortalized in a scene in The Blues Brothers. These days, the market sets up on nearby Desplaines Street (between Roosevelt and Howard) on the first and third Sundays of every month, where visitors will find vendors hawking their wares, an abundance of delicious Mexican food and occasional performances by local bands and dance troupes. Don't let the cold or wet weather scare you away—the Maxwell Street Market takes place outdoors year-round.

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